3-Methyl-1-phenyl-4-[(phen­yl)(2-phenyl­hydrazin-1-yl)meth­ylidene]-1H-pyrazol-5(4H)-one

Idemudia, O.G.; Sadimenko, A.P.; Afolayan, A.J.; Hosten, E.C.

doi:10.1107/S1600536812013463

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1280-o1281

doi:10.1107/S1600536812013463

Open

access

3-Methyl-1-phenyl-4-[(phenyl)(2-phenylhydrazin-1-yl)methylidene]-1H-pyrazol-5(4H)-one

Omoruyi G. Idemudia,^a ^* Alexander P. Sadimenko,^a Anthony J. Afolayan ^a and Eric C. Hosten ^b

^aUniversity of Fort Hare, Department of Chemistry, Private Bag X1314, Alice 5700, South Africa, and ^bNelson Mandela Metropolitan University, Department of Chemistry, PO Box 77000, Port Elizabeth 6031, South Africa
^*Correspondence e-mail: idemudiaog@yahoo.com

(Received 15 March 2012; accepted 28 March 2012; online 4 April 2012)

The title compound, C₂₃H₂₀N₄O, is a heterocyclic phenylhydrazone Schiff base with a pyrazole moiety. In the crystal, a variety of interactions occur, including N—H⋯π and π–π stacking between the phenyl ring of the phenylhydrazinyl group and its symmetry-generated equivalent [centroid–centroid distance = 3.6512 (7) Å].

Related literature

For related structures, see: Zhu et al. (2010 , 2011 ); Goh et al. (2009 ). For general background to pyrazolones and their applications, see: Yang et al. (2000 ); Konstantinovic et al. (2008 ); Joshi et al. (2011 ); Turan-Zitouni et al. (2000 ). For the biological activities of hydrazone Schiff bases, see: Yadav et al. (2010 ); Ozdemir et al. (2008 ); Vicini et al. (2006 ); Jagadeesh et al. (2010 ); Walcourt et al. (2004 ) and for their catalytic abilities, see: Pouralimardan et al. (2007 ).

Experimental

Crystal data

C₂₃H₂₀N₄O
M_r = 368.43
Monoclinic, P 2₁ /c
a = 8.6806 (2) Å
b = 20.4319 (4) Å
c = 10.6100 (2) Å
β = 99.713 (1)°
V = 1854.83 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 200 K
0.59 × 0.40 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: numerical (SADABS; Bruker, 2010 ) T_min = 0.87, T_max = 0.98
17965 measured reflections
4607 independent reflections
3891 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.04
4607 reflections
262 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯Cg2ⁱ	0.887 (18)	2.728 (17)	3.5021 (12)	146.6 (14)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and ShelXle (Hübschle et al., 2011 ); molecular graphics: ORTEP-3 (Farrugia,1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812013463/zj2068sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013463/zj2068Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013463/zj2068Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812013463/zj2068Isup4.cml

checkCIF report

Comment top

Hydrazone Schiff bases, a product of the condensation reaction of hydrazine derivatives and a carbonyl via nucleophilic addition reaction represents an important group of compounds due to their chelating properties and numerous applications. Antimicrobial (Yadav et al., 2010; Ozdemir et al., 2008), antitumour (Vicini et al., 2006), antioxidant (Jagadeesh et al., 2010), antimalarial (Walcourt et al., 2004) and catalytic (Pouralimardan et al., 2007) activities, amidst others. Heterocyclic Schiff bases derived from pyrazolone have been well documented (Yang et al., 2000). A new heterocyclic phenylhydrazone Schiff base with pyrazolyl moeity is prepared and its crystal structure reported herein (Fig.1).

In the crystal structure π stacking occurs between the phenyls of adjacent phenylhydazone groups with a centroid to centroid distance of 3.6512 (7) Å and slippage of 0.922 Å (Fig. 2). The dihedral angles formed by the least square planes between the phenyl of the phenylhydrazone group with the pyrazole and the C21—C26 aromatic ring are 85.29 (6)° and 77.88 (6)° repectively. The phenyl on the pyrazole group is slight twisted out of the pyrazole plane by 12.84 (4)°.

Intra molecular C—H···N, C—H···O and N—H···O interactions occur while inter molecular interactions include C—H···O, phenyl hydrazone pi stacking and N—H···π interactions (Fig. 2 - for clarity the N—H···π interaction is not shown).

The packing of the title compound is shown in Figure 3.

Related literature top

For related structures, see: Zhu et al. (2010, 2011); Goh et al. (2009). For general background to and applications of pyrazolones, see: Yang et al. (2000); Konstantinovic et al. (2008); Joshi et al. (2011); Turan-Zitouni et al. (2000). For the biological activity of hydrazone Schiff bases, see: Yadav et al. (2010); Ozdemir et al. (2008); Vicini et al. (2006); Jagadeesh et al. (2010); Walcourt et al. (2004) and for their catalytic ability, see: Pouralimardan et al. (2007).

Experimental top

A mixture of phenylhydrazine and 4-benzoyl-3-methyl-1-phenyl-2-pyrazoline-5-one (ratio 1:1) in methanol was refluxed for 5 h. The mixture was poured into cold distilled water to precipitate the yellow titled compound (yield: 92%; m.p: 190–192°C), which was isolated by filtration and recrystalized from methanol. Single crystals of the titled compound suitable for X-ray diffraction was obtained from methanol by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and ShelXle (Hübschle et al., 2011); molecular graphics: ORTEP-3 (Farrugia,1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anistropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Inter and intra molecular contacts as well as the short ring interaction between C31—C36 and C31ⁱ—C36ⁱ (blue dashed line). Symmetry operators: ⁱ -x + 1, -y, -z + 2.
	Fig. 3. Molecular packing of the title compound, viewed along [1 0 0].

3-Methyl-1-phenyl-4-[(phenyl)(2-phenylhydrazin-1-yl)methylidene]-1H- pyrazol-5(4H)-one top

Crystal data top

C₂₃H₂₀N₄O	F(000) = 776
M_r = 368.43	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 464 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.6806 (2) Å	Cell parameters from 200 reflections
b = 20.4319 (4) Å	θ = 2.6–26.6°
c = 10.6100 (2) Å	µ = 0.08 mm⁻¹
β = 99.713 (1)°	T = 200 K
V = 1854.83 (7) Å³	Block, yellow
Z = 4	0.59 × 0.40 × 0.22 mm

Data collection top

Bruker APEXII CCD diffractometer	4607 independent reflections
Radiation source: sealed tube	3891 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.3°, θ_min = 2.4°
ϕ and ω scans	h = −11→11
Absorption correction: numerical (SADABS; Bruker, 2010)	k = −27→26
T_min = 0.87, T_max = 0.98	l = −14→14
17965 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0506P)² + 0.492P] where P = (F_o² + 2F_c²)/3
4607 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₃H₂₀N₄O	V = 1854.83 (7) Å³
M_r = 368.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6806 (2) Å	µ = 0.08 mm⁻¹
b = 20.4319 (4) Å	T = 200 K
c = 10.6100 (2) Å	0.59 × 0.40 × 0.22 mm
β = 99.713 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4607 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2010)	3891 reflections with I > 2σ(I)
T_min = 0.87, T_max = 0.98	R_int = 0.014
17965 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.27 e Å⁻³
4607 reflections	Δρ_min = −0.17 e Å⁻³
262 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.37112 (10)	−0.06816 (4)	0.56481 (8)	0.0415 (2)
N1	0.19594 (11)	−0.06784 (5)	0.37026 (8)	0.0317 (2)
N2	0.08885 (10)	−0.02411 (5)	0.30147 (9)	0.0326 (2)
N3	0.35993 (12)	0.04986 (5)	0.68161 (8)	0.0351 (2)
H3	0.3866 (18)	0.0073 (8)	0.6855 (14)	0.049 (4)*
N4	0.42974 (12)	0.09280 (5)	0.77706 (8)	0.0333 (2)
H4	0.529 (2)	0.0996 (8)	0.7705 (16)	0.055 (4)*
C1	0.27317 (13)	−0.04046 (6)	0.48275 (9)	0.0314 (2)
C2	0.21562 (12)	0.02578 (5)	0.48023 (9)	0.0301 (2)
C3	0.10127 (12)	0.03072 (5)	0.36586 (10)	0.0308 (2)
C4	−0.00114 (14)	0.08688 (6)	0.31689 (12)	0.0410 (3)
H4A	0.0612	0.1205	0.2829	0.062*
H4B	−0.048	0.1054	0.3868	0.062*
H4C	−0.084	0.0717	0.2488	0.062*
C5	0.27016 (12)	0.07110 (5)	0.57521 (9)	0.0295 (2)
C11	0.22094 (13)	−0.12928 (5)	0.31617 (10)	0.0318 (2)
C12	0.31193 (16)	−0.17665 (6)	0.38711 (12)	0.0422 (3)
H12	0.356	−0.1683	0.4738	0.051*
C13	0.33855 (19)	−0.23605 (7)	0.33154 (14)	0.0521 (3)
H13	0.4021	−0.268	0.3802	0.063*
C14	0.27385 (18)	−0.24925 (7)	0.20636 (14)	0.0516 (3)
H14	0.291	−0.2903	0.1692	0.062*
C15	0.18389 (16)	−0.20201 (7)	0.13574 (12)	0.0477 (3)
H15	0.1397	−0.2108	0.0493	0.057*
C16	0.15679 (14)	−0.14194 (6)	0.18873 (11)	0.0390 (3)
H16	0.0953	−0.1097	0.1389	0.047*
C21	0.23894 (12)	0.14208 (5)	0.56126 (10)	0.0316 (2)
C22	0.29871 (15)	0.17609 (6)	0.46630 (11)	0.0410 (3)
H22	0.3529	0.1533	0.4092	0.049*
C23	0.27886 (18)	0.24303 (7)	0.45546 (14)	0.0526 (4)
H23	0.3216	0.2665	0.3922	0.063*
C24	0.19696 (19)	0.27574 (7)	0.53651 (15)	0.0575 (4)
H24	0.1834	0.3218	0.5289	0.069*
C25	0.13434 (18)	0.24193 (7)	0.62892 (15)	0.0534 (4)
H25	0.0757	0.2647	0.683	0.064*
C26	0.15687 (14)	0.17513 (6)	0.64279 (12)	0.0401 (3)
H26	0.1164	0.1521	0.7078	0.048*
C31	0.40268 (12)	0.07932 (5)	0.90166 (9)	0.0275 (2)
C32	0.51420 (13)	0.09944 (5)	1.00413 (10)	0.0314 (2)
H32	0.6078	0.1197	0.989	0.038*
C33	0.48897 (14)	0.08995 (6)	1.12813 (10)	0.0348 (2)
H33	0.5649	0.1043	1.1978	0.042*
C34	0.35439 (14)	0.05974 (6)	1.15146 (10)	0.0364 (2)
H34	0.3384	0.0525	1.2368	0.044*
C35	0.24276 (13)	0.04011 (6)	1.04931 (11)	0.0359 (2)
H35	0.1497	0.0196	1.0651	0.043*
C36	0.26506 (13)	0.05003 (5)	0.92422 (10)	0.0314 (2)
H36	0.1873	0.037	0.8547	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0531 (5)	0.0408 (5)	0.0266 (4)	0.0052 (4)	−0.0043 (3)	−0.0013 (3)
N1	0.0352 (5)	0.0358 (5)	0.0233 (4)	−0.0036 (4)	0.0026 (3)	−0.0006 (3)
N2	0.0315 (4)	0.0386 (5)	0.0269 (4)	−0.0043 (4)	0.0028 (3)	0.0017 (4)
N3	0.0482 (6)	0.0343 (5)	0.0215 (4)	−0.0007 (4)	0.0023 (4)	−0.0021 (4)
N4	0.0386 (5)	0.0394 (5)	0.0217 (4)	−0.0079 (4)	0.0048 (4)	−0.0014 (4)
C1	0.0365 (5)	0.0374 (6)	0.0207 (4)	−0.0040 (4)	0.0056 (4)	−0.0008 (4)
C2	0.0332 (5)	0.0359 (5)	0.0218 (5)	−0.0031 (4)	0.0068 (4)	0.0012 (4)
C3	0.0295 (5)	0.0375 (6)	0.0261 (5)	−0.0053 (4)	0.0069 (4)	0.0019 (4)
C4	0.0387 (6)	0.0424 (6)	0.0394 (6)	0.0009 (5)	−0.0008 (5)	0.0016 (5)
C5	0.0316 (5)	0.0359 (5)	0.0224 (4)	−0.0033 (4)	0.0089 (4)	0.0011 (4)
C11	0.0338 (5)	0.0360 (5)	0.0268 (5)	−0.0089 (4)	0.0091 (4)	−0.0031 (4)
C12	0.0570 (7)	0.0376 (6)	0.0313 (6)	−0.0038 (5)	0.0048 (5)	−0.0010 (5)
C13	0.0703 (9)	0.0385 (7)	0.0465 (7)	0.0016 (6)	0.0069 (7)	−0.0017 (6)
C14	0.0616 (8)	0.0440 (7)	0.0502 (8)	−0.0049 (6)	0.0126 (6)	−0.0145 (6)
C15	0.0476 (7)	0.0586 (8)	0.0366 (6)	−0.0082 (6)	0.0065 (5)	−0.0175 (6)
C16	0.0371 (6)	0.0493 (7)	0.0304 (5)	−0.0048 (5)	0.0051 (4)	−0.0060 (5)
C21	0.0338 (5)	0.0342 (5)	0.0258 (5)	−0.0055 (4)	0.0022 (4)	−0.0003 (4)
C22	0.0480 (7)	0.0428 (7)	0.0318 (6)	−0.0101 (5)	0.0057 (5)	0.0034 (5)
C23	0.0622 (9)	0.0438 (7)	0.0465 (7)	−0.0173 (6)	−0.0060 (6)	0.0118 (6)
C24	0.0667 (9)	0.0340 (6)	0.0615 (9)	−0.0028 (6)	−0.0189 (7)	0.0021 (6)
C25	0.0573 (8)	0.0465 (7)	0.0519 (8)	0.0131 (6)	−0.0036 (6)	−0.0093 (6)
C26	0.0403 (6)	0.0444 (7)	0.0355 (6)	0.0027 (5)	0.0060 (5)	−0.0009 (5)
C31	0.0333 (5)	0.0267 (5)	0.0226 (4)	0.0014 (4)	0.0050 (4)	0.0004 (4)
C32	0.0326 (5)	0.0336 (5)	0.0276 (5)	−0.0032 (4)	0.0040 (4)	−0.0001 (4)
C33	0.0404 (6)	0.0378 (6)	0.0246 (5)	0.0008 (4)	0.0006 (4)	−0.0015 (4)
C34	0.0463 (6)	0.0387 (6)	0.0258 (5)	0.0029 (5)	0.0110 (4)	0.0029 (4)
C35	0.0374 (6)	0.0359 (6)	0.0367 (6)	−0.0030 (4)	0.0132 (4)	0.0021 (4)
C36	0.0334 (5)	0.0309 (5)	0.0293 (5)	−0.0029 (4)	0.0030 (4)	−0.0019 (4)

Geometric parameters (Å, º) top

O1—C1	1.2456 (13)	C15—C16	1.3865 (18)
N1—C1	1.3844 (13)	C15—H15	0.95
N1—N2	1.4021 (13)	C16—H16	0.95
N1—C11	1.4123 (14)	C21—C26	1.3856 (16)
N2—C3	1.3072 (14)	C21—C22	1.3941 (15)
N3—C5	1.3316 (14)	C22—C23	1.381 (2)
N3—N4	1.3983 (13)	C22—H22	0.95
N3—H3	0.899 (16)	C23—C24	1.378 (2)
N4—C31	1.4084 (13)	C23—H23	0.95
N4—H4	0.887 (17)	C24—C25	1.383 (2)
C1—C2	1.4414 (16)	C24—H24	0.95
C2—C5	1.3915 (15)	C25—C26	1.3832 (19)
C2—C3	1.4358 (14)	C25—H25	0.95
C3—C4	1.4903 (16)	C26—H26	0.95
C4—H4A	0.98	C31—C32	1.3903 (14)
C4—H4B	0.98	C31—C36	1.3925 (15)
C4—H4C	0.98	C32—C33	1.3834 (15)
C5—C21	1.4782 (15)	C32—H32	0.95
C11—C12	1.3880 (17)	C33—C34	1.3801 (17)
C11—C16	1.3968 (15)	C33—H33	0.95
C12—C13	1.3856 (19)	C34—C35	1.3858 (16)
C12—H12	0.95	C34—H34	0.95
C13—C14	1.379 (2)	C35—C36	1.3881 (15)
C13—H13	0.95	C35—H35	0.95
C14—C15	1.380 (2)	C36—H36	0.95
C14—H14	0.95

C1—N1—N2	111.93 (9)	C14—C15—H15	119.4
C1—N1—C11	128.62 (9)	C16—C15—H15	119.4
N2—N1—C11	119.25 (9)	C15—C16—C11	119.29 (12)
C3—N2—N1	106.56 (9)	C15—C16—H16	120.4
C5—N3—N4	121.98 (10)	C11—C16—H16	120.4
C5—N3—H3	117.6 (10)	C26—C21—C22	120.10 (11)
N4—N3—H3	119.8 (10)	C26—C21—C5	121.36 (10)
N3—N4—C31	115.89 (9)	C22—C21—C5	118.50 (10)
N3—N4—H4	110.4 (11)	C23—C22—C21	119.83 (13)
C31—N4—H4	115.0 (11)	C23—C22—H22	120.1
O1—C1—N1	126.39 (11)	C21—C22—H22	120.1
O1—C1—C2	129.28 (10)	C24—C23—C22	119.92 (13)
N1—C1—C2	104.33 (9)	C24—C23—H23	120.0
C5—C2—C3	131.87 (10)	C22—C23—H23	120.0
C5—C2—C1	122.48 (10)	C23—C24—C25	120.39 (13)
C3—C2—C1	105.65 (9)	C23—C24—H24	119.8
N2—C3—C2	111.45 (10)	C25—C24—H24	119.8
N2—C3—C4	119.07 (10)	C26—C25—C24	120.19 (14)
C2—C3—C4	129.46 (10)	C26—C25—H25	119.9
C3—C4—H4A	109.5	C24—C25—H25	119.9
C3—C4—H4B	109.5	C25—C26—C21	119.52 (13)
H4A—C4—H4B	109.5	C25—C26—H26	120.2
C3—C4—H4C	109.5	C21—C26—H26	120.2
H4A—C4—H4C	109.5	C32—C31—C36	119.81 (9)
H4B—C4—H4C	109.5	C32—C31—N4	118.15 (9)
N3—C5—C2	118.43 (10)	C36—C31—N4	121.94 (9)
N3—C5—C21	118.41 (9)	C33—C32—C31	120.08 (10)
C2—C5—C21	123.10 (9)	C33—C32—H32	120.0
C12—C11—C16	119.55 (11)	C31—C32—H32	120.0
C12—C11—N1	120.79 (10)	C34—C33—C32	120.52 (10)
C16—C11—N1	119.64 (10)	C34—C33—H33	119.7
C13—C12—C11	120.03 (12)	C32—C33—H33	119.7
C13—C12—H12	120.0	C33—C34—C35	119.38 (10)
C11—C12—H12	120.0	C33—C34—H34	120.3
C14—C13—C12	120.75 (14)	C35—C34—H34	120.3
C14—C13—H13	119.6	C34—C35—C36	120.91 (10)
C12—C13—H13	119.6	C34—C35—H35	119.5
C13—C14—C15	119.17 (13)	C36—C35—H35	119.5
C13—C14—H14	120.4	C35—C36—C31	119.28 (10)
C15—C14—H14	120.4	C35—C36—H36	120.4
C14—C15—C16	121.20 (12)	C31—C36—H36	120.4

C1—N1—N2—C3	2.24 (12)	C11—C12—C13—C14	−0.9 (2)
C11—N1—N2—C3	−173.08 (9)	C12—C13—C14—C15	1.1 (2)
C5—N3—N4—C31	127.25 (11)	C13—C14—C15—C16	−0.5 (2)
N2—N1—C1—O1	177.77 (10)	C14—C15—C16—C11	−0.44 (19)
C11—N1—C1—O1	−7.46 (18)	C12—C11—C16—C15	0.69 (17)
N2—N1—C1—C2	−2.98 (11)	N1—C11—C16—C15	179.00 (10)
C11—N1—C1—C2	171.79 (10)	N3—C5—C21—C26	−64.01 (14)
O1—C1—C2—C5	2.00 (18)	C2—C5—C21—C26	118.77 (12)
N1—C1—C2—C5	−177.23 (9)	N3—C5—C21—C22	113.82 (12)
O1—C1—C2—C3	−178.25 (11)	C2—C5—C21—C22	−63.40 (14)
N1—C1—C2—C3	2.53 (11)	C26—C21—C22—C23	1.41 (18)
N1—N2—C3—C2	−0.47 (11)	C5—C21—C22—C23	−176.45 (11)
N1—N2—C3—C4	−179.01 (9)	C21—C22—C23—C24	−1.53 (19)
C5—C2—C3—N2	178.40 (10)	C22—C23—C24—C25	0.0 (2)
C1—C2—C3—N2	−1.33 (11)	C23—C24—C25—C26	1.6 (2)
C5—C2—C3—C4	−3.25 (19)	C24—C25—C26—C21	−1.7 (2)
C1—C2—C3—C4	177.03 (11)	C22—C21—C26—C25	0.22 (18)
N4—N3—C5—C2	174.74 (10)	C5—C21—C26—C25	178.02 (11)
N4—N3—C5—C21	−2.61 (15)	N3—N4—C31—C32	152.77 (10)
C3—C2—C5—N3	169.52 (11)	N3—N4—C31—C36	−30.79 (15)
C1—C2—C5—N3	−10.79 (15)	C36—C31—C32—C33	0.46 (16)
C3—C2—C5—C21	−13.26 (17)	N4—C31—C32—C33	176.98 (10)
C1—C2—C5—C21	166.43 (10)	C31—C32—C33—C34	0.88 (17)
C1—N1—C11—C12	13.08 (17)	C32—C33—C34—C35	−1.32 (18)
N2—N1—C11—C12	−172.48 (10)	C33—C34—C35—C36	0.44 (18)
C1—N1—C11—C16	−165.22 (11)	C34—C35—C36—C31	0.89 (17)
N2—N1—C11—C16	9.22 (15)	C32—C31—C36—C35	−1.33 (16)
C16—C11—C12—C13	−0.05 (19)	N4—C31—C36—C35	−177.71 (10)
N1—C11—C12—C13	−178.35 (12)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.899 (16)	1.994 (16)	2.7204 (13)	136.9 (13)
C12—H12···O1	0.95	2.26	2.8993 (15)	124
C16—H16···N2	0.95	2.46	2.7950 (16)	100
C33—H33···O1ⁱ	0.95	2.59	3.3094 (13)	132
N4—H4···Cg2ⁱⁱ	0.887 (18)	2.728 (17)	3.5021 (12)	146.6 (14)

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₄O
M_r	368.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	8.6806 (2), 20.4319 (4), 10.6100 (2)
β (°)	99.713 (1)
V (Å³)	1854.83 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.59 × 0.40 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Numerical (SADABS; Bruker, 2010)
T_min, T_max	0.87, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	17965, 4607, 3891
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.04
No. of reflections	4607
No. of parameters	262
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.17

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and ShelXle (Hübschle et al., 2011), ORTEP-3 (Farrugia,1997) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cg2ⁱ	0.887 (18)	2.728 (17)	3.5021 (12)	146.6 (14)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The authors would like to thank the Department of Chemistry and the Govan Mbeki Research and Development Centre (GMRDC), both of the University of Fort Hare, for their support.

References

Bruker (2010). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra,, Rai, N. S. & Kalluraya, B. (2009). Acta Cryst. E65, o3099–o3100. Google Scholar
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281–1284. Web of Science CrossRef IUCr Journals Google Scholar
Jagadeesh, P. K., Himajaa, M., Malib, S. V., Ranjithaa, A., Karigarc, A. & Sikarward, M. (2010). J. Pharm. Res. 3, 2460–2462. Google Scholar
Joshi, K. T., Pancholi, A. M., Pandya, K. S. & Thakar, A. S. (2011). J. Chem. Pharm. Res. 3, 741–749. CAS Google Scholar
Konstantinovic, S. S., Kapor, A., Radovanovic, B. C. & Deak, A. (2008). CI&CEQ, 14, 27–34. CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ozdemir, A., Turan-Zitouni, G., Kaplancikli, Z. A., Demirci, F. & Iscan, G. J. (2008). J. Enzyme Inhib. Med. Chem. 23, 470–475. Web of Science PubMed CAS Google Scholar
Pouralimardan, O., Chamayou, A., Janiak, C. & Monfared, H. (2007). Inorg. Chim. Acta, 360, 1599–1608. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Turan-Zitouni, G., Chevallet, P., Kiliç, F. S. & Erol, K. (2000). Eur. J. Med. Chem. 35, 635–641. Web of Science PubMed CAS Google Scholar
Vicini, P., Incerti, M., Doytchinova, I. A., Colla, P. L., Busonera, B. & Loddo, R. E. (2006). Eur. J. Med. Chem. 41, 624–632. Web of Science CrossRef PubMed CAS Google Scholar
Walcourt, A., Loyevsky, M., Lovejoy, D. B., Gordeuk, V. R. & Richardson, D. R. (2004). Int. J. Biochem. Cell Biol. 36, 401–407. Web of Science CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yadav, J., Pandeya, S. N., Nath, G. & Singh, S. P. (2010). J. Chem. Pharm. Res. 2, 558–563. CAS Google Scholar
Yang, Z. Y., Yang, R. D., Li, F. S. & Yu, K. B. (2000). Polyhedron, 19, 2599–2604. Web of Science CSD CrossRef CAS Google Scholar
Zhu, H., Ban, L., Zhang, P., Zhao, X. & Ren, J. (2011). Acta Cryst. E67, o476–o477. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, H., Wei, Z., Bu, L., Xu, X. & Shi, J. (2010). Acta Cryst. E66, m904. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1280-o1281

doi:10.1107/S1600536812013463

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Methyl-1-phenyl-4-[(phen­yl)(2-phenyl­hydrazin-1-yl)meth­yl­idene]-1H-pyrazol-5(4H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Methyl-1-phenyl-4-[(phenyl)(2-phenylhydrazin-1-yl)methylidene]-1H-pyrazol-5(4H)-one